1-Butyne is anorganic compound with the formulaCH3CH2C≡CH. It is aterminal alkyne. The compound is a common terminal alkyne substrate in diverse studies of catalysis. It is a colorless combustiblegas.[2] In 2017, 3.9 million pounds (1,700 long tons) was produced in the USA.[4]
 | |
 | |
| Names | |
|---|---|
| Preferred IUPAC name But-1-yne | |
| Other names Ethylacetylene Ethylethyne, UN 2452 | |
| Identifiers | |
| |
3D model (JSmol) | |
| ChEBI | |
| ChemSpider |
|
| ECHA InfoCard | 100.003.139 |
| EC Number |
|
| UNII | |
| UN number | 2452 |
| |
| |
| Properties[2] | |
| C4H6 | |
| Molar mass | 54.091 g/mol |
| Odor | Acetylenic[1] |
| Density | 0.6783 g cm−3[2] |
| Melting point | −125.7 °C (−194.3 °F; 147.5 K)[2] |
| Boiling point | 8.08 °C (46.54 °F; 281.23 K)[2] |
| Hazards | |
| GHS labelling: | |
 | |
| Danger | |
| H220 | |
| P210,P377,P381,P403 | |
| Flash point | 7°C (45°F)[3] |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
1-Butyne participates in reactions typical for terminal alkynes, such asalkyne metathesis,[5] hydrogenation, condensation withformaldehyde. Based on itsheat of combustion, it is slightly more stable than its isomer2-butyne.[6]
The combustion of 1-Butyne producespropargyl radicals, a pre-cursor tosoot andpolycyclic aromatic hydrocarbons, as the propargyl radicals can form basicaromatic rings, making butyne's fuel usage a concern for emissions.[7]
1-Butyne is in unsatutared C4 petroleum cuts, and has to be separated out in industrial hydrorefining to make1-butene, which is used to makelow density polyethylene andpolybutene.Distillation is impractical due to similar boiling points, so 1-butyne is removed by catalytic hydrogenation.[8] Usually thecatalyst ispalladium, operated with liquid hydrocarbon andhydrogen gas at 20-60°C and pressures up to 10 bar.[9]
See also
editReferences
edit- ^"Safety Data Sheet: Ethyl Acetylene"(PDF). Airgas. 19 August 2019. Retrieved2 April 2025.
- ^abcdeLide, David R. (2008).CRC Handbook of Chemistry and Physics, 89th Edition.CRC Press. pp. 3–84.ISBN 978-0-8493-0488-0.
- ^Gangolli, S.. (2005).Dictionary of Substances and Their Effects (DOSE, 3rd Electronic Edition). Royal Society of Chemistry (RSC).Retrieved from here
- ^EPA, US."US EPA: Chemical Data Reporting: 1-Butyne".chemview.epa.gov. Retrieved2 April 2025.
- ^Zhang, Wei; Kraft, Stefan; Moore, Jeffrey S. (2004). "Highly Active Trialkoxymolybdenum(VI) Alkylidyne Catalysts Synthesized by a Reductive Recycle Strategy".Journal of the American Chemical Society.126 (1):329–335.doi:10.1021/ja0379868.PMID 14709099.
- ^Prosen, E.J.; Maron, F.W.; Rossini, F.D. (1951)."Heats of combustion, formation, and insomerization of ten C4 hydrocarbons".Journal of Research of the National Bureau of Standards.46 (2): 106.doi:10.6028/jres.046.015.
- ^Lu, Haitao; Dong, Shijun; Liu, Fuqiang; Nagaraja, Shashank S.; Lindblade, Nathan; Turner, Mattias A.; Mathieu, Olivier; Petersen, Eric L.; Vilchez, Jesús Caravaca; Heufer, Karl Alexander; Xu, Gang; Sarathy, S. Mani; Curran, Henry J. (1 January 2023)."A wide-range experimental and kinetic modeling study of the pyrolysis and oxidation of 1-butyne".Proceedings of the Combustion Institute.39 (1):355–364.doi:10.1016/j.proci.2022.09.044. Retrieved2 April 2025.
- ^García Colli, G.; Alves, J. A.; Martínez, O. M.; Barreto, G. F. (1 August 2019). "Application of a catalytic membrane reactor to the selective hydrogenation of 1-Butyne".Chemical Engineering and Processing - Process Intensification.142: 107518.doi:10.1016/j.cep.2019.04.018.
- ^Alves, J. A.; Bressa, S. P.; Martínez, O. M.; Barreto, G. F. (15 January 2007)."Kinetic study of the liquid-phase hydrogenation of 1-butyne over a commercial palladium/alumina catalyst".Chemical Engineering Journal.125 (3):131–138.doi:10.1016/j.cej.2006.08.006.
External links
edit | This article about ahydrocarbon is astub. You can help Wikipedia byexpanding it. |